data_04src1124
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H23 N O6'
_chemical_formula_sum
 'C18 H23 N O6'
_chemical_formula_weight          349.37
_chemical_absolute_configuration  unk
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)
_symmetry_space_group_name_hall   'P 2yb'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    8.713(4)
_cell_length_b                    6.582(4)
_cell_length_c                    15.739(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.70(5)
_cell_angle_gamma                 90.00
_cell_volume                      883.9(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2032
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        blade
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              372
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9432
_exptl_absorpt_correction_T_max   0.9990
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   '10cm confocal mirrors'
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             3834
_diffrn_reflns_av_R_equivalents   0.0000
_diffrn_reflns_av_sigmaI/netI     0.0564
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.37
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3834
_reflns_number_gt                 3081
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0180P)²+0.1542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.059(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3834
_refine_ls_number_parameters      233
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0811
_refine_ls_R_factor_gt            0.0570
_refine_ls_wR_factor_ref          0.1043
_refine_ls_wR_factor_gt           0.0983
_refine_ls_goodness_of_fit_ref    1.380
_refine_ls_restrained_S_all       1.379
_refine_ls_shift/su_max           0.028
_refine_ls_shift/su_mean          0.004
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.2646(3) 0.2188(4) 0.26490(17) 0.0292(6) Uani 1 1 d . . .
C2 C 0.0914(3) 0.2235(4) 0.22181(16) 0.0287(6) Uani 1 1 d . . .
H2 H 0.0490 0.0832 0.2252 0.034 Uiso 1 1 calc R . .
C3 C 0.0700(3) 0.2788(4) 0.12533(17) 0.0350(7) Uani 1 1 d . . .
H3A H -0.0422 0.3058 0.1015 0.042 Uiso 1 1 calc R . .
H3B H 0.1293 0.4045 0.1194 0.042 Uiso 1 1 calc R . .
C4 C 0.1262(4) 0.1103(5) 0.0738(2) 0.0473(8) Uani 1 1 d . . .
H4A H 0.2391 0.0903 0.0944 0.071 Uiso 1 1 calc R . .
H4B H 0.1053 0.1473 0.0122 0.071 Uiso 1 1 calc R . .
H4C H 0.0706 -0.0157 0.0814 0.071 Uiso 1 1 calc R . .
C5 C -0.0002(3) 0.3658(4) 0.27106(16) 0.0288(6) Uani 1 1 d . . .
H5 H -0.1123 0.3216 0.2577 0.035 Uiso 1 1 calc R . .
C6 C 0.0032(3) 0.5912(4) 0.25300(19) 0.0352(6) Uani 1 1 d . . .
H6A H -0.0445 0.6151 0.1912 0.042 Uiso 1 1 calc R . .
H6B H -0.0623 0.6619 0.2883 0.042 Uiso 1 1 calc R . .
C7 C 0.0176(3) 0.1729(4) 0.40121(17) 0.0298(6) Uani 1 1 d . . .
C8 C 0.0958(3) 0.1620(4) 0.49688(17) 0.0338(6) Uani 1 1 d . . .
H8A H 0.1337 0.2981 0.5183 0.041 Uiso 1 1 calc R . .
H8B H 0.0201 0.1135 0.5315 0.041 Uiso 1 1 calc R . .
C9 C 0.2311(3) 0.0165(4) 0.50499(17) 0.0332(6) Uani 1 1 d . . .
C10 C 0.4502(3) -0.0486(4) 0.44083(18) 0.0351(6) Uani 1 1 d . . .
H10A H 0.4097 -0.1893 0.4397 0.042 Uiso 1 1 calc R . .
H10B H 0.5508 -0.0416 0.4833 0.042 Uiso 1 1 calc R . .
C11 C 0.4736(3) 0.0134(4) 0.35089(17) 0.0290(6) Uani 1 1 d . . .
H11 H 0.5320 0.1450 0.3552 0.035 Uiso 1 1 calc R . .
C12 C 0.5683(3) -0.1503(4) 0.31574(17) 0.0332(6) Uani 1 1 d . . .
H12A H 0.6726 -0.1599 0.3547 0.040 Uiso 1 1 calc R . .
H12B H 0.5151 -0.2826 0.3179 0.040 Uiso 1 1 calc R . .
C13 C 0.5914(3) -0.1166(4) 0.22453(17) 0.0325(6) Uani 1 1 d . . .
C14 C 0.5938(3) -0.2822(5) 0.17060(19) 0.0385(7) Uani 1 1 d . . .
H14 H 0.5741 -0.4143 0.1903 0.046 Uiso 1 1 calc R . .
C15 C 0.6245(3) -0.2573(5) 0.0880(2) 0.0459(8) Uani 1 1 d . . .
H15 H 0.6274 -0.3726 0.0520 0.055 Uiso 1 1 calc R . .
C16 C 0.6509(3) -0.0668(5) 0.0580(2) 0.0459(8) Uani 1 1 d . . .
H16 H 0.6728 -0.0499 0.0017 0.055 Uiso 1 1 calc R . .
C17 C 0.6452(3) 0.0996(5) 0.1107(2) 0.0438(7) Uani 1 1 d . . .
H17 H 0.6615 0.2320 0.0901 0.053 Uiso 1 1 calc R . .
C18 C 0.6157(3) 0.0750(4) 0.19335(19) 0.0370(7) Uani 1 1 d . . .
H18 H 0.6121 0.1907 0.2290 0.044 Uiso 1 1 calc R . .
N1 N 0.3203(2) 0.0392(3) 0.29420(14) 0.0290(5) Uani 1 1 d . . .
O1 O 0.34634(19) 0.3744(3) 0.27137(12) 0.0371(5) Uani 1 1 d . . .
O2 O 0.1549(2) 0.6783(3) 0.27084(15) 0.0467(6) Uani 1 1 d . . .
H2A H 0.2215 0.5892 0.2657 0.070 Uiso 1 1 calc R . .
O3 O 0.05707(19) 0.3434(3) 0.36495(11) 0.0294(4) Uani 1 1 d . . .
O4 O -0.0631(2) 0.0409(3) 0.36339(12) 0.0333(4) Uani 1 1 d . . .
O5 O 0.2399(2) -0.1468(3) 0.54011(13) 0.0432(5) Uani 1 1 d . . .
O6 O 0.33888(19) 0.0915(3) 0.46430(12) 0.0331(4) Uani 1 1 d . . .
H1N H 0.258(3) -0.067(5) 0.2880(17) 0.035(8) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 O1 1.240(3) . ?
C1 N1 1.325(3) . ?
C1 C2 1.524(3) . ?
C2 C3 1.536(4) . ?
C2 C5 1.538(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.513(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 O3 1.468(3) . ?
C5 C6 1.512(4) . ?
C5 H5 1.0000 . ?
C6 O2 1.416(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O4 1.198(3) . ?
C7 O3 1.335(3) . ?
C7 C8 1.523(4) . ?
C8 C9 1.504(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O5 1.204(3) . ?
C9 O6 1.334(3) . ?
C10 O6 1.440(3) . ?
C10 C11 1.526(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.457(3) . ?
C11 C12 1.528(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.384(4) . ?
C13 C18 1.385(4) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1N 0.88(3) . ?
O2 H2A 0.8400 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 C1 N1 123.0(2) . . ?
O1 C1 C2 121.4(2) . . ?
N1 C1 C2 115.6(2) . . ?
C1 C2 C3 110.8(2) . . ?
C1 C2 C5 110.9(2) . . ?
C3 C2 C5 112.5(2) . . ?
C1 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
C5 C2 H2 107.5 . . ?
C4 C3 C2 111.7(2) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 C6 105.8(2) . . ?
O3 C5 C2 109.93(19) . . ?
C6 C5 C2 118.1(2) . . ?
O3 C5 H5 107.5 . . ?
C6 C5 H5 107.5 . . ?
C2 C5 H5 107.5 . . ?
O2 C6 C5 114.4(2) . . ?
O2 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
O2 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
O4 C7 O3 125.0(2) . . ?
O4 C7 C8 123.8(2) . . ?
O3 C7 C8 111.1(2) . . ?
C9 C8 C7 107.4(2) . . ?
C9 C8 H8A 110.2 . . ?
C7 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O5 C9 O6 124.4(2) . . ?
O5 C9 C8 125.7(3) . . ?
O6 C9 C8 109.8(2) . . ?
O6 C10 C11 106.9(2) . . ?
O6 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O6 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
N1 C11 C10 108.7(2) . . ?
N1 C11 C12 110.8(2) . . ?
C10 C11 C12 109.3(2) . . ?
N1 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C12 C11 H11 109.3 . . ?
C13 C12 C11 115.3(2) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C18 118.5(3) . . ?
C14 C13 C12 119.3(3) . . ?
C18 C13 C12 122.1(2) . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.7(3) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C1 N1 C11 122.9(2) . . ?
C1 N1 H1N 119.7(18) . . ?
C11 N1 H1N 116.4(18) . . ?
C6 O2 H2A 109.5 . . ?
C7 O3 C5 116.76(19) . . ?
C9 O6 C10 117.5(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.239
_refine_diff_density_min   -0.210
_refine_diff_density_rms    0.052
